A radical approach to araliopsine and related quinoline alkaloids using manganese(III) acetate

G  Bar; A F  Parsons; C B  Thomas

A radical approach to araliopsine and related quinoline alkaloids using manganese(III) acetate

G Bar, A F Parsons, C B Thomas

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Reaction of 4-hydroxy-1-methyl-2(1H)-quinolone 3 with electron-rich alkenes and manganese(III) acetate produces tricyclic quinoline alkaloids, including araliopsine 1, in one-pot reactions. This combined intermolecular addition-cyclisation reaction produces angular and/or linear tricycles and the regioselectivity of the cyclisation is shown to depend on whether alkyl or aryl substituents are attached to the alkene. (C) 2000 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	7751-7755
Number of pages	5
Journal	Tetrahedron Letters
Volume	41
Issue number	40
Publication status	Published - 30 Sept 2000

Keywords

alkaloids
manganese and compounds
quinolines
radicals and radical reactions
1,3-DICARBONYL COMPOUNDS
CYCLIZATIONS

Cite this

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title = "A radical approach to araliopsine and related quinoline alkaloids using manganese(III) acetate",

abstract = "Reaction of 4-hydroxy-1-methyl-2(1H)-quinolone 3 with electron-rich alkenes and manganese(III) acetate produces tricyclic quinoline alkaloids, including araliopsine 1, in one-pot reactions. This combined intermolecular addition-cyclisation reaction produces angular and/or linear tricycles and the regioselectivity of the cyclisation is shown to depend on whether alkyl or aryl substituents are attached to the alkene. (C) 2000 Elsevier Science Ltd. All rights reserved.",

keywords = "alkaloids, manganese and compounds, quinolines, radicals and radical reactions, 1,3-DICARBONYL COMPOUNDS, CYCLIZATIONS",

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T1 - A radical approach to araliopsine and related quinoline alkaloids using manganese(III) acetate

AU - Bar, G

AU - Parsons, A F

AU - Thomas, C B

PY - 2000/9/30

Y1 - 2000/9/30

N2 - Reaction of 4-hydroxy-1-methyl-2(1H)-quinolone 3 with electron-rich alkenes and manganese(III) acetate produces tricyclic quinoline alkaloids, including araliopsine 1, in one-pot reactions. This combined intermolecular addition-cyclisation reaction produces angular and/or linear tricycles and the regioselectivity of the cyclisation is shown to depend on whether alkyl or aryl substituents are attached to the alkene. (C) 2000 Elsevier Science Ltd. All rights reserved.

AB - Reaction of 4-hydroxy-1-methyl-2(1H)-quinolone 3 with electron-rich alkenes and manganese(III) acetate produces tricyclic quinoline alkaloids, including araliopsine 1, in one-pot reactions. This combined intermolecular addition-cyclisation reaction produces angular and/or linear tricycles and the regioselectivity of the cyclisation is shown to depend on whether alkyl or aryl substituents are attached to the alkene. (C) 2000 Elsevier Science Ltd. All rights reserved.

KW - alkaloids

KW - manganese and compounds

KW - quinolines

KW - radicals and radical reactions

KW - 1,3-DICARBONYL COMPOUNDS

KW - CYCLIZATIONS

M3 - Article

SN - 0040-4039

VL - 41

SP - 7751

EP - 7755

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 40

ER -